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Pending
    • $699,000

    21 Overlook Drive, Pawling, NY 12564

    3beds
    1,460sqft
    Single Family Residence, Residential
    Built in 1968
    4.5 Acres Lot
    $-- Zestimate®
    $479/sqft
    $-- HOA

    What's special

    A rare Pawling hilltop retreat with panoramic views & endless potential! Opportunities like this are extraordinarily hard to come by. Perched high to capture breathtaking, miles-long panoramic vistas, this true "sunset house" offers an idyllic Hudson Valley lifestyle centered around big skies, rolling hills, and complete tranquility. Imagine sitting on the expansive covered patio with your favorite beverage looking out into the vibrant sunset, or lounging by the crystal-clear in-ground pool, sunbathing while overlooking nearby farms and sparkling lakes. This property was built for unforgettable outdoor living and limitless entertaining. Inside, the home is a clean-cut, light-filled ranch featuring three bedrooms and two-and-a-half bathrooms. The expansive living room serves as the heart of the home with its classic brick wood-burning fireplace, two huge picture windows framing the valley skyline, and sliding glass doors that open directly onto the massive patio. Adjacent, the kitchen is outfitted with high-end cabinetry and modern stainless steel appliances, opening seamlessly to a bright dining area framed by another impressive picture window. The primary bedroom offers its own private half bath, while a hallway closet conveniently houses the main-level laundry. Downstairs, the finished walk-out basement expands your living space with two versatile rooms perfect for a home theater, gym, or guest quarters, complemented by a full bathroom and abundant storage space. Spanning over 4.5 acres, the grounds offer exceptional privacy along with rare long-term flexibility. Whether you envision expanding the existing home or exploring options to subdivide and sell or build a second residence, this property delivers a quintessential Pawling sanctuary where indoor ease meets endless horizon.
    39 days
    1,410
    112

    Zillow last checked:

    Listing updated:

    Listed by:

    McGrath Realty Inc 845-855-5550,

    Colleen McGrath 845-803-4341,

    Brian McGrath 845-721-0940,

    McGrath Realty Inc

    Source: OneKey® MLS as distributed by MLS GRID,MLS#: 1029600MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 3
      • Bathrooms: 3
      • Full bathrooms: 2
      • 1/2 bathrooms: 1
      Bedroom 1
      • Level: First
      Bedroom 2
      • Level: First
      Bedroom 3
      • Level: First
      Bathroom 1
      • Level: First
      Bathroom 2
      • Level: First
      Bathroom 3
      • Level: Basement
      Bonus room
      • Level: Basement
      Family room
      • Level: First
      Kitchen
      • Level: First
      Heating
      • Oil
      Cooling
      • Central Air
      Appliances
      • Included: Dishwasher, Dryer, Electric Range, Microwave, Refrigerator, Stainless Steel Appliance(s), Washer, Indirect Water Heater
      • Laundry: In Hall, Inside
      Features
      • First Floor Bedroom, First Floor Full Bath, Beamed Ceilings
      • Flooring: Carpet, Hardwood, Tile
      • Windows: Casement, Oversized Windows, Skylight(s)
      • Basement: See Remarks,Storage Space,Walk-Out Access
      • Attic: None
      • Number of fireplaces: 1
      • Fireplace features: Living Room, Wood Burning
      Interior area
      • Total structure area: 2,908
      • Total interior livable area: 1,460 sqft
      Video & virtual tour

      Property

      Parking
      • Total spaces: 4
      • Parking features: Driveway, Garage, Heated Garage, Oversized
      • Garage spaces: 2
      • Has uncovered spaces: Yes
      Features
      • Levels: One
      • Patio & porch: Covered, Patio
      • Exterior features: Garden, Mailbox, Rain Gutters
      • Has private pool: Yes
      • Pool features: Diving Board, Fenced, In Ground, Outdoor Pool
      • Has view: Yes
      • View description: Mountain(s), Neighborhood, Panoramic, Skyline
      Lot
      • Size: 4.5 Acres
      • Features: Back Yard, Cleared, Front Yard, Garden, Landscaped, Near Golf Course, Near Public Transit, Near School, Near Shops, Private, Secluded, Sloped, Split Possible, Sprinklers In Rear, Stone/Brick Wall, Views
      • Residential vegetation: Partially Wooded
      Details
      • Additional structures: Shed(s)
      • Parcel number: 1340896956004707460000
      • Special conditions: None
      • Other equipment: Pool Equip/Cover

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Ranch
      • Property subtype: Single Family Residence, Residential
      Materials
      • Aluminum Siding, Block, Frame
      • Foundation: Block
      Condition
      • Year built: 1968
      • Major remodel year: 1968

      Utilities & green energy

      • Sewer: Septic Tank
      • Water: Well
      • Utilities for property: Cable Connected, Electricity Connected, Phone Connected, Propane, Trash Collection Private

      Community & HOA

      HOA
      • Has HOA: No
      Location
      • Region: Pawling

      Financial & listing details

      • Price per square foot: $479/sqft
      • Tax assessed value: $137,600
      • Annual tax amount: $10,222
      • Date on market: 7/31/2026
      • Cumulative days on market: 36 days
      • Listing agreement: Exclusive Right To Sell
      • Electric utility on property: Yes

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        8/28/2026Pending sale$699,000$479/sqft
        Source: OneKey® MLS as distributed by MLS GRID #1029600 Report a problem
        7/31/2026Listed for sale$699,000$479/sqft
        Source: OneKey® MLS as distributed by MLS GRID #1029600 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025-- $137,600
        2024-- $137,600
        2023-- $137,600
        2022-- $137,600
        2021-- $137,600
        2020-- $137,600
        2019-- $137,600
        2018-- $137,600
        2017$8,314 $137,600
        2016-- $137,600
        2015-- $137,600
        2014-- $137,600
        2012-- $137,600
        2011-- $137,600
        2010-- $137,600
        2009-- $137,600
        2008-- $137,600
        2007-- $137,600
        2006-- $137,600
        2005-- $137,600
        2004-- $137,600
        2003-- $137,600
        2002-- $137,600
        2001-- $137,600
        2000-- $137,600
        Find assessor info on the county website

        Monthly payment

        Estimated monthly payment$1,822
        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
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        Climate risks

        Neighborhood: 12564

        Getting around

        0 / 100
        Car-Dependent

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Pawling Elementary School
        • Middle: Pawling Middle School
        • High: Pawling High School

        Source: OneKey® MLS as distributed by MLS GRID. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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